title: The effect of the isomers of alpha-cholorohydrin and racemic beta-chlorolactate on the rat kidney.
abstract: The (R)- and (S)-isomers of the male antifertility agent alpha-chlorohydrin have been synthesized. When administered to rats, the (R)-isomer induced a period of diuresis and glucosuria, whereas the (S)-isomer, which possesses the antifertility activity, had no detrimental action on the kidney. Neither of the isomers of alpha-chlorohydrin nor those of an active analogue, 3-amino-1-chloropropan-2-ol, had any inhibitory activity on the oxidative metabolism of glucose or lactate in isolated kidney tubules. However, beta-chlorolactate, a metabolite common to both compounds, inhibited the oxidation of glucose, lactate, pyruvate and glutamate to CO2. It is proposed that the antifertility action of the (S)-isomers of alpha-chlorohydrin and 3-amino-1-chloropropan-2-ol is unrelated to the renal toxicity of the (R)-isomers, a toxic action involving the inhibition of oxidative metabolism by (S)-beta-chlorolactate or a further product of this metabolite.
mesh_terms: D000818:Animals; D002245:Carbon Dioxide / Q000378:metabolism; D002728:Chlorohydrins / Q000494:pharmacology / Q000633:toxicity*; D004231:Diuresis / Q000187:drug effects; D006029:Glycosuria / Q000139:chemically induced; D007536:Isomerism; D007668:Kidney / Q000187:drug effects*; D007773:Lactates / Q000633:toxicity*; D008099:Liver / Q000187:drug effects; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D000517:alpha-Chlorohydrin / Q000633:toxicity*
chemical_list: D002728:Chlorohydrins; D007773:Lactates; D002245:Carbon Dioxide; C007000:3-chlorolactate; C009721:CL 88236; D000517:alpha-Chlorohydrin